


Snakes and Dragons

by TheManWithAPurpleTopHat



Series: RadioSnake Discord Spice Event [1]
Category: Hazbin Hotel (Web Series)
Genre: Demisexual Alastor (Hazbin Hotel), Established Relationship, Fluff and Smut, Loss of Virginity, M/M, Smut, Virgin Alastor (Hazbin Hotel)
Language: English
Status: Completed
Published: 2020-05-04
Updated: 2020-05-04
Packaged: 2021-03-02 18:27:21
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,111
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24001312
Author URL: https://archiveofourown.org/users/TheManWithAPurpleTopHat/pseuds/TheManWithAPurpleTopHat
Summary: The first prompt for the Radiosnake Spice event: Alastor Losing His Virginity
Relationships: Alastor/Sir Pentious (Hazbin Hotel)
Series: RadioSnake Discord Spice Event [1]
Series URL: https://archiveofourown.org/series/1730854
Comments: 4
Kudos: 99





	Snakes and Dragons

**Author's Note:**

> This took me a lot longer than I thought it would to finish, I got absolutely zero sleep last night XD
> 
> EDIT: I've rewritten a few key parts and corrected spelling and grammar errors I found after posting. The major changes were made after reviewing feedback from some readers in the discord server. Theses edits are as follows:  
> 1) I've changed the part about this being Alastor's first erection. I've been informed this was wildly unrealistic  
> 2) I've also been informed it's highly unlikely Alastor would be able to cum without having his dick touched during his first time, so I've added that detail to the scene

"You never answered me."

Sir Pentious huffed out a sigh, wiping up the last remnants of the spilled tea. Of course they  _ had _ to be drinking Rooibos this evening; he was never going to get the damn stain out of that tablecloth. "I was a bit busy trying not to choke on my tea."

"Yes, I noticed that." A slight head tilt, eyes blinking with the closest they ever came to innocence. "You didn’t exactly succeed in that, I’m sorry to say. Why exactly did you feel the need to spit out half a cup of tea?"

“Why did  _ you _ feel the need to ask ssomething like  _ that _ right as I was taking a sssip!?” He could feel a slight warmth pooling in his cheeks, though the advantage of being cold blooded and covered in scales was that he never blushed very visibly. “No, I have a better question. Why are you assking about such things at all!?”

Alastor lifted his hands and shrugged, grinning softly into his cup. “It’s not exactly a rare topic of discuss, you know,” he said, “As a matter of fact, most of Hell seems obsessed with the concept. You can hardly get through a day without hearing some reference to it.”

“Yes, I know that. But it is a shocking thing to hear come out of  _ your  _ mouth. What even brought this on?”

There was a pause, a moment of thoughtful silence as Alastor took a sip of his tea. Sir Pentious studied his partner’s face carefully, searching the countless little lines and curves for any signal that something was troubling the Radio Demon. The man seemed the perfect portrait of nonchalance, but that only worried the serpent.

Alastor cleared his throat, making a few small mechanical sounds as he set the cup down. “I’m well aware that this is highly unusual coming from me, though I thought the spit-take was a bit much, dear. I’ve been thinking on this for a few months, working out the best way to bring it up.”

“And of all the ways you could have possibly brought it up, you decided to go with ‘Ssay, darling, how would you like to make whoopee tonight?’”

“...Well when you say it with that tone in your voice it sounds silly.”

“You looked me in the eyes and the words make whoopee left your mouth. Make. Whoopee. And you wonder why I spit my tea out.”

“And how would you prefer I phrase it? I see no reason to be vulgar about this. Any other phrasing and I imagine I’ll be turned off the idea entirely. Unless of course this is your way of saying you don’t want to do it? I won’t mind in the slightest if you’d rather not, we can make another pot of tea and forget the whole thing. Perhaps put a few records on before bed?”

Sir Pentious cleared his throat, averting his gaze. “It’s not that I’m turning down your...offer. It’s just that the offer is so unlike you. I’ve known you for over seventy years, and this is the first you’ve ever expressed interest in having your corn ground.”

A laugh track burst from Alastor’s microphone before abruptly cutting off with a discordant screech, the equipment’s owner stifling a cough. “Pardon that, nerves,” he said with a sheepish grin, “I’ve never heard that one, it’s certainly...graphic, but in a polite way. I’ll have to remember it, if the night goes well. But I digress. You see, my dear, all my life I’ve been quite happy with my...corn in tact. It’s not that I’ve been exactly saving my corn for a special occasion as some do, I simply never met anyone I wanted to grind it, had no interest in even looking for that in a companion.”

The snake demon nodded. “You’ve always made that quite clear, dearest.”

The two exchanged soft smiles at that. In the fifty odd years they’d courted and grown intimate, there had always been the established understanding that neither of them wanted nor expected a fast-paced relationship. Sir Pentious was quite content following Alastor’s request that they use the bed purely for sleeping- when they shared a bed at all, which was not a guarantee every night.

“Yes, well that seems to have changed in recent times, I’d say it started roughly a year or two ago. It took me some time to realize that’s what I was experiencing, but I’ve finally come to the conclusion I would like to try horizontal refreshments with you. With your permission, of course.”

Silence met Alastor’s declaration as the two men stared at each other. The Radio Demon looked at his partner expectantly, not pressing for an answer but certainly prepared to wait until he got one. Had this been a joke, he might have dropped the matter once Sir Pentious's shock had worn off. Was this some kind of test? He wouldn’t put it past Alastor to proposition him for the sole purpose of seeing how he would react, finding out if Sir Pentious was secretly hoping to copulate with him but never mentioned it. And if he was being completely honest…

“If you’re sure you’d like to try it, I would like that as well,” he declared, watching Alastor’s reaction carefully.

His partner seemed to jump ever so slightly, blinking a few times as his smile grew wider. “Wonderful,” he said, “I admit I wasn’t expecting you to say yes. ...So, shall we?”

“You want to do it right now?”

“Yes...no. In a few hours. I need time to set everything up.” What exactly he meant by that both intrigued and worried Sir Pentious. There was no telling what Alastor could have planned-hold on. Alastor couldn’t plan this! The man had never had sex before, he had no idea how to set the mood or what supplies they were going to need for this.

“I have a better idea.” Sir Pentious stood, gathering their teacups. “Go upstairs and have a nice relaxing bath, give me about an hour. I’ll gather everything we’ll need and set the scene for us. I dare say I’d do a better job than you would. After all, I have experience on my side.~”

Alastor huffed, his eyes narrowing slightly. He might have looked almost threatening were it not for the scarlet flush covering his face. “Very well,” he said, “This is the one, and the  _ only _ one subject of which I will admit you are the more knowledgeable. And it’s only because it never interested me enough to spend time learning the logistics and mechanics!”

The snake gave a triumphant laugh, his forked tongue flicking out as he grinned. “Worry not, my sweet, I shall make sure we do this right. Your first time shall be passionate, classy, with no small amount of style. How do you feel about scented candles?~”

“...It depends on where you intend to put them.”

The Radio Demon had to duck to avoid the teacup thrown at his head.

* * *

Alastor didn’t put his suit back on as he normally did after a bath, instead wrapping himself up in a plush red bathrobe. His chest fluttered as he patted himself dry and prepared to open the door to the bedroom, feeling something akin to the thrill just before he went on the air for an important performance. Taking a deep breath to steady his nerves, he pushed the door open.

The first thing that greeted Alastor’s senses was a light fragrance of cinnamon and cedarwood, presumably wafting from the gently flickering candles that bathed the room in dim light. Somewhere unseen, a phonograph was playing Your Red Lips, a sweet yet lively piece from 1929. He tapped a hoof in time with the beat as he looked around. A trail of white rose petals lead from his place at the door to the bed, which had been redecorated with deep purple curtains shrouding it in shadows. Alastor assumed his partner was waiting for him in those shadows, as he couldn’t see the snake anywhere. Sir Pentious as asked him a few questions through the door as he’d been bathing, namely his preferences on scents, material for the sheets, his opinion on penetration… 

He was roused from his thoughts by a hiss startlingly close to him. Looking to his left, Alastor felt heat rise to his face as he took in the sight of Sir Pentious towering over him, eyes glowing intensely and hissing softly. He was completely naked, even his hat was nowhere to be seen. A strange scent was coming off the snake’s body, mingling with the smoke to fill Alastor’s senses with a soft haze. The deer demon watched as Sir Pentious lifted a clawed hand to cup his cheek, gently stroking it with a thumb.

“Look down.”

The command was like a jolt of energy that shot through Alastor’s gut, making his heart race and his mouth go dry. His gaze slowly traveled down from Sir Pentious’s sharp stare, past his broad chest and lightly toned abdomen. He took in a soft gasp when his eyes met with a pair of considerably large dicks protruding from his partner’s waist. Both were a soft yellow at the base that faded to a deep fuschia, much like the eyes that decorated the tail below them. Small pearls of liquid leaked from their tips, and they seemed to throb slightly as he stared at them.

Sir Pentious let out a low chortle as he looked at Alastor’s expression, reaching out to massage the man’s shoulders. Alstor leaned into the touch, though he kept his gaze fixed upon the snake’s groin.

“I’ve given some thought as to the best position to do thiss.” Alastor’s ear twitched, watching silently as his partner slowly circled him, pulling him closer by his shoulders. “I’ve concluded we’ll have the most luck with what was known in my day as St. George. Allow me to explain, my dear.” Sir Pentious leaned in until his mouth hovered just above Alastor’s ear. “You will be playing the part of Ssssaint George, and you will be riding a dragon.~”

“H-haha… I hardly qualify for any sort of sainthood, sweetheart.” Alastor’s voice came out a bit higher than usual, the heat in his face steadily growing. “And if memory serves, St. George didn’t ride a dragon, he killed one.”

“Not when I’m telling the story, he doesn’t,” Sir Pentious hissed darkly, and Alastor’s knees nearly gave out.

“Shall we...get started, then?” he asked softly, looking up when he was met with another laugh.

“So eager, aren’t you?~” Sir Pentious grinned, leading Alastor to the bed, “Are you that excited about this?”

Alastor sputtered, looking away. He hadn’t expected this at all. Sir Pentious had seemed so flustered and uncertain when he’d first proposed the idea. Now, it seemed his attitude had completely changed. Of course, Alastor had seen his partner in similar moods countless times, but this was somehow vastly different from his usual teasing or darker style of flirtation. In the space of an hour he’d transformed into some dark and mysterious incubus, ready to lay Alastor down and ravage him if only given the chance.

If the Radio Demon had thought himself even remotely prepared for this when he’d entered the room, such a notion was long gone from his mind now.

As they came closer to the bed, Alastor noticed the sheets were covered in more white petals and in some places entire rose blossoms. In the center of the bed on a crimson pillow was a small black vial that seemed to contain some sort of thick, sweet-smelling liquid. Sir Pentious took this vial, dipping his fingers into its contents.

“Get comfortable, my sweet,” he instructed, and Alastor climbed into the bed as a shiver ran down his spine. His heart pounded in his chest as he watched Sir Pentious position himself between Alastor’s legs, bracing on one arm so he could lay on top of the deer demon.

It began much like one of their more passionate sessions of kissing and cuddling, with a few bites here and there. Alastor melted under his beloved’s touch, wrapping his arms around the snake’s neck with a content sigh. He tensed for a moment when felt a hand massage his hips, taking a deep breath to steady himself.

Thanks to the strange substance Sir Pentious had coated his fingers in, there wasn’t much trouble getting the first finger in. Alastor gasped and twitched at first, his leg kicking a few times when a claw would brush over something particularly sensitive. He could hear Sir Pentious talking, but by the time the second finger joined in he wasn’t paying any attention to the serpent’s voice. He began to feel a hot tension coiling like a spring in his groin, and flushed when he looked down. His own erection met his curious gaze, and he had to stifle a laugh.

“Would ya look at that.”

“Trussst me, I am.~”

Alastor shuddered at the almost hungry tone in his beloved’s voice. Is this what his prey felt as he stalked them down, overpowering them and devouring them? It was a thrill that set every nerve in his body on fire, and his dick throbbed at the image of Sir Pentious hunting him like a predator. Like a dragon.

“I believe that would be a sign I’m doing my job well, is it not?~”   
  
Alastor groaned softly, leaning back against the pillows. “I haven’t the slightest idea what you’re doing or how you’re doing it, but I am enjoying myself.”   
  


“Clearly,” Sir Pentious laughed, then hummed in thought as he carefully removed his claws. “Would you say you’re ready for the next part?”

His face was more red than his hair now, he was sure of it. Alastor nodded, taking a deep breath. “I’m ready, my love.”

“Then get up for a moment, let me take your place there.”

Alastor did as he was told, turning his attention back upon the erections decorating the serpent’s body. He watched as Sir Pentious applied a copious amount of lubricant to one of them, his tail twitching with excitement.

“You may get on top of me whenever you’re ready, darling,” Sir Pentious said, his fangs glistening as he grinning at the shivering deer. Alastor could feel the blush all the way in his ears now, his head swimming as he straddled the massive tail of his beloved. With a few instructions, he was properly positioned, his breath catching in his throat as he felt the tip of Sir Pentious’s dick press gently against his body.

As he slowly lowered himself down on the serpent’s cock, Alastor’s eyes grew wider. He didn’t move a muscle once it was in, his mouth hanging open as he stared at the headboard. His thighs clenched around the large tail beneath him, and the snake had to hold back a groan at the hot pressure constricting his dick.

“O-Oh my.”

He blinked in surprise when he heard a laugh under him, looking down at Sir Pentious as if he’d temporarily forgotten the serpent was in the room with him. His partner was reclined casually against a small mountain of pillows, his hood falling in gentle waves around his face and shoulders.

“How does it feel, my love?”

Alastor paused, considering the question. “It feels...full,” he stated, whining softly, “Very full. And warm.”

“You’re not giggling, I take it you’re not in any pain?”

The deer shook his head, rolling his hips experimentally then gasping at the result. He trembled as cool hands held his hips steady, massaging them lightly.

“There’s no rush, my dear, we have all the time in the world.~”

Sir Pentious needn’t have bothered there. Once Alastor worked out a motion that sent waves of hot pleasure coursing through his body, he didn’t keep a slow pace for long. Ever the hedonist, he devoured this newfound source of pleasure with wild abandon, gasping and moaning with each frantic rock of his hips. The sound of his lovers groans and enraptured hisses caused him to melt, falling forward to crash his lips against Sir Pentious’s in a passionate kiss. When the snake began thrusting his hips upwards in time with his movements, Alastor could barely remember to breathe.

Soon their moans were enough to drown out the record playing, and the mattress creaked under their enthusiastic rolls and thrusts. The bathrobe was abandoned, slipping of Alastor’s shoulders and forgotten amongst the sweaty sheets and scattered pillows. They could hardly care less about the mess they were making of the bed, too fixated on the building pressure filling them to the point of madness. Alastor looked down at his lover, the snake panting and rolling under him, fangs bared in a kin to a snarl and his eyes squeezed tightly shut. The sight of his lover unravelling under him sent another jolt of hot pleasure down his spine, and he couldn’t hold back any longer. As he reached down to clumsily paw and stroke at his throbbing erection, his orgasm crashed down on him like a bolt of lightning. He threw his head back and screamed, static filling his vision as pleasure overwhelmed him.

Alastor’s chest heaved as he slowly came back down, staring into space with a half-lidded gaze. He was so lost in his own postorgasmic high, he barely even registered the feeling of cum trailing down his stomach and his thighs. He tilted his head when heard another moan below him.

“You make the most adorable sounds when you’re losing yourself in passion, my love,” Sir Pentious stated with a smirk. “I love it.~”

The deer whined, covering his face to hide the deep blush. He squealed as he was pulled down into a warm embrace, the dick inside of him carefully slipping out and retreating back into its slit. He sighed in content, pressing closer to the soft chest of his lover as he felt a set of claws gently card through his hair.

“Once we’ve cleaned up, shall we retire for the night?” the snake suggested.

“Hm...I’m not that sleepy, really,” Alastor confessed, pulling aside a curtain to look out the window, “It’s not very late, by the looks of the sky. We could stay up for a bit, perhaps watch a picture show together?”

Sir Pentious nodded, smiling softly as he placed a soft kiss on Alastor’s forehead. He eyed his lover warily when the deer began giggling, looking very pleased with himself. “What horrid thought has popped into that head of yours thisss time?”

“We should make popcorn.”

**Author's Note:**

> As hard as it was to complete, I did have a lot of fun writing this. It's wildly self-indulgent and probably very out of character, but I wrote it in under three days where a fic this length usually takes me weeks  
> At any rate, I hope y'all enjoyed reading!


End file.
